Best Holiday Giveaways in Lexington, KY: 2026 Local Guide
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Lexington's 2026 holiday season includes six giveaway programs: daily radio drawings, downtown shopping incentives, luxury item packages, and holiday market raffles—with opportunities for everyone.
Lexington offers at least six active holiday giveaway opportunities for 2026, from daily radio drawings to downtown shopping incentives and special event prizes. Whether you prefer a chance to win gift cards, luxury items, or unique experiences, several programs run through the season with different entry methods and eligibility requirements. Holiday giveaways in Lexington range from low-barrier (listening to a radio station) to participation-based (shopping at downtown businesses or attending events).
Most require no purchase or have minimal entry thresholds, though age restrictions apply to some programs.
Verification note: Program terms and availability can change. This page was checked against linked sources on September 23, 2026.
Daily Radio Drawings at Christmas 105.5
Christmas 105.5 FM runs daily giveaway drawings throughout the holiday season, with winners drawn at 2 pm daily. The Lexington radio station awards gift cards from Kentucky Branded and other vendors to daily winners. No purchase is necessary to enter—listeners can tune in during contest periods or submit entries through the station's website.
Downtown Lexington's Shop and Celebrate Cash Prizes
Downtown Lexington Partnership's "Shop and Celebrate" program offers weekly cash prizes and a $500 grand prize, with entries triggered by spending $25 or more at participating downtown businesses. Participants text "downtown" to enter the system; the program runs through the holiday season and is presented by Central Bank. Eligibility requires being 21 or older to enter.
Bluegrass Hospitality Group also runs a companion promotion offering a $20 certificate for every $100 in gift cards purchased at participating restaurants and bars, beginning November 13.
Luxury Item Giveaway at My Favorite Things
My Favorite Things in Lexington (2721 Old Rosebud Road) offers a holiday giveaway package worth approximately $7,000, including a Spartina tote filled with luxury home décor and gifts. The store specializes in luxury furniture, unique gifts, and interior design consultation. Entry details are available from the store directly.
Giveaways at Holiday Attractions and Markets
Southern Lights at Kentucky Horse Park features holiday giveaways nightly November 27–December 31, 2026 (closed Christmas Day), from 5:30–10:00 pm, with over one million twinkling lights, Santa photos, and model trains. General admission is $35 per carload; Keeneland's Bucky mascot appears for giveaway opportunities. Three concurrent holiday markets operate December 6–7, 2026: the Holly Day Market at Alltech Arena (Kentucky Horse Park), the Woodland Triangle Holiday Shop Hop featuring $1,500+ in raffle prizes across 12 local shops, and Wildside Winery's Christmas Market with live music. These markets combine shopping with prize drawings, giving attendees multiple chances to win.
How Entry Methods and Eligibility Work
Most Lexington giveaways fall into three entry categories: no-purchase listening (Christmas 105.5), purchase-based participation (Shop and Celebrate requires $25 minimum spending), and event attendance (Southern Lights, holiday markets). Age restrictions apply only to Shop and Celebrate (21+) and venue entry fees vary ($35 for Southern Lights per carload; most markets are free to attend). Daily radio drawings and shop-hop raffles typically have no separate entry deadline, while event-based giveaways run through specific dates.
Frequently Asked Questions
Do I have to make a purchase to enter most of these giveaways?
No. Christmas 105.5 requires only listening; Southern Lights charges $35 admission but includes the giveaway with entry. Shop and Celebrate requires $25 spending at participating businesses.
My Favorite Things and holiday markets have their own entry methods—check directly with each venue.
Which giveaway has the highest prize value?
My Favorite Things' package is valued at approximately $7,000, the largest single prize listed. Shop and Celebrate's $500 grand prize is the second-largest guaranteed prize.
When do most of these giveaways end?
Most programs run through December 2026. Southern Lights ends December 31; holiday markets run December 6–7. Christmas 105.5 and Shop and Celebrate run "through the holiday season"—confirm specific end dates with each program before entering.